Methyl iodide → Ethyl 2-(pyridin-4-yl)propanoate

Temperature

-10 °C

A solution of ethyl 2-(pyridin-4-yl)acetate (1.00 g, 6.06 mmol) in THF (10 ml) was added dropwise to a suspension of sodium hydride (0.24 g, 6.06 mmol, 60%) in THF (10 ml) at −50° C. under an atmosphere of nitrogen. The reaction mixture was stirred for 1 h. Methyl iodide (2.10 ml, 33.6 mmol) in THF (10 ml) was added slowly at −50° C. over a period of 15 min, then the reaction mixture was warmed up to −10° C. and continued to stir for another 4 h. The reaction mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine (50 ml), dried over anhydrous sodium sulfate, filtered and concentrated under vacuo. The crude was washed with diethyl ether (10 ml) to get 550 mg (50.7%) of ethyl 2-(pyridin-4-yl)propanoate as a colorless liquid.

1. stirringto stir for another 4 h
2. customThe reaction mixture was quenched with aqueous ammonium chloride
3. extractionextracted with ethyl acetate (2×50 ml)
4. washThe combined organic extracts were washed with brine (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under vacuo
8. washThe crude was washed with diethyl ether (10 ml)

ORD record

ord-b2a7646453604093a4b139ada6cd393a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067888B2